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PE20040779A1 - DERIVATIVES OF 1- (4-BENZYL-PIPERAZIN-1-IL) -3-PHENYL-PROPENONE - Google Patents

DERIVATIVES OF 1- (4-BENZYL-PIPERAZIN-1-IL) -3-PHENYL-PROPENONE

Info

Publication number
PE20040779A1
PE20040779A1 PE2003001076A PE2003001076A PE20040779A1 PE 20040779 A1 PE20040779 A1 PE 20040779A1 PE 2003001076 A PE2003001076 A PE 2003001076A PE 2003001076 A PE2003001076 A PE 2003001076A PE 20040779 A1 PE20040779 A1 PE 20040779A1
Authority
PE
Peru
Prior art keywords
phenyl
cyane
oxopropenyl
methylpiperazin
fluorobenzyl
Prior art date
Application number
PE2003001076A
Other languages
Spanish (es)
Inventor
Birgit Bollbuck
Jorg Eder
Richard Heng
Lazlo Revesz
Achim Schlapbach
Rudolf Walchli
Original Assignee
Novartis Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Novartis Ag filed Critical Novartis Ag
Publication of PE20040779A1 publication Critical patent/PE20040779A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Transplantation (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

SE REFIERE A COMPUESTOS DERIVADOS 1-(4-BENCIL-PIPERAZIN-1-IL)-3-FENIL-PROPENONA DE LA FORMULA I, O UNA SAL O ESTER FARMACEUTICAMENTE ACEPTABLE DEL MISMO, EN DONDE R1 ES X-R10, X-(R10)2, ENTRE OTROS; R2 Y R7 SON H, CIANO, HALOGENO, NITRO U OXILO OPCIONALMENTE SUSTITUIDO, ENTRE OTROS; R3 Y R4 SON H, CIANO, HALOGENO, ALQUILO, ENTRE OTROS; R5 Y R6 SON H, CIANO, ALQUILO, ALQUENILO, ENTRE OTROS; X ES UN ENLAZADOR CON UNO HASTA 4 ATOMOS SELECCIONADOS DE N, C, O o S; Y DONDE, CUANDO ESTE ENLAZADOR COMPRENDE DOS O MAS CARBONOS, EL ENLAZADOR PUEDE TENER UNO O MAS ENLACES C=C o C///C; R10 ES H, CIANO, NITRO u OXILO OPCIONALMENTE SUSTITUIDO, ENTRE OTROS. SON COMPUESTOS PREFERIDOS: N-(5-CLORO-2-[(E)-3-[(R)-4-(4-FLUOROBENCIL)-2-METILPIPERAZIN-1-IL]-3-OXOPROPENIL]FENIL)-N´-CIANOGUANIDINA; N-(5-CLORO-2-[(E)-3-[(R)-4-(4-FLUOROBENCIL)-2-METILPIPERAZIN-1-IL]-3-OXOPROPENIL]FENIL)-ACETAMIDA; N-(5-CLORO-2-[(E)-3-[(S)-4-(4-FLUOROBENCIL)-2-METILPIPERAZIN-1-IL)-3-OXOPROPENIL]FENIL)-ACETAMIDA; ENTRE OTROS. TAMBIEN SE REFIERE A UN PROCESO PARA SU FABRICACION Y UNA COMPOSICION FARMACEUTICA QUE LOS CONTIENE. ESTOS COMPUESTOS SON INHIBIDORES DE LOS RECEPTORES DE QUIMIOCINA Y SON UTILES PARA TRATAR ENFERMEDADES O DESORDENES QUE INVOLUCRAN LA MIGRACION Y ACTIVACION DE MONOCITOS Y CELULAS T, INCLUYENDO ENFERMEDADES INFLAMATORIASREFERS TO COMPOUNDS DERIVED 1- (4-BENZYL-PIPERAZIN-1-IL) -3-PHENYL-PROPENONE OF FORMULA I, OR A PHARMACEUTICALLY ACCEPTABLE SALT OR ESTER OF THE SAME, WHERE R1 IS X-R10, X- ( R10) 2, AMONG OTHERS; R2 AND R7 ARE H, CYANE, HALOGEN, NITRO OR OPTIONALLY SUBSTITUTED OXYL, AMONG OTHERS; R3 AND R4 ARE H, CYANE, HALOGEN, ALKYL, AMONG OTHERS; R5 AND R6 ARE H, CYANE, ALKYL, ALKENYL, AMONG OTHERS; X IS A LINKER WITH UP TO 4 ATOMS SELECTED FROM N, C, O, or S; AND WHERE, WHEN THIS LINKER INCLUDES TWO OR MORE CARBONS, THE LINKER MAY HAVE ONE OR MORE LINKS C = C or C /// C; R10 IS H, CYANE, NITRO, OR OXYL, OPTIONALLY REPLACED, AMONG OTHERS. PREFERRED COMPOUNDS ARE: N- (5-CHLORINE-2 - [(E) -3 - [(R) -4- (4-FLUOROBENZYL) -2-METHYLPIPERAZIN-1-IL] -3-OXOPROPENYL] PHENYL) -N ´-CYANOGUANIDINE; N- (5-CHLORO-2 - [(E) -3 - [(R) -4- (4-FLUOROBENZYL) -2-METHYLPIPERAZIN-1-IL] -3-OXOPROPENYL] PHENYL) -ACETAMIDE; N- (5-CHLORO-2 - [(E) -3 - [(S) -4- (4-FLUOROBENZYL) -2-METHYLPIPERAZIN-1-IL) -3-OXOPROPENYL] PHENYL) -ACETAMIDE; AMONG OTHERS. IT ALSO REFERS TO A PROCESS FOR THEIR MANUFACTURE AND A PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM. THESE COMPOUNDS ARE INHIBITORS OF CHEMOKINE RECEPTORS AND ARE USEFUL TO TREAT DISEASES OR DISORDERS INVOLVING MIGRATION AND ACTIVATION OF MONOCYTES AND T-CELLS, INCLUDING INFLAMMATORY DISEASES

PE2003001076A 2002-10-25 2003-10-23 DERIVATIVES OF 1- (4-BENZYL-PIPERAZIN-1-IL) -3-PHENYL-PROPENONE PE20040779A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB0224917.5A GB0224917D0 (en) 2002-10-25 2002-10-25 Organic compounds

Publications (1)

Publication Number Publication Date
PE20040779A1 true PE20040779A1 (en) 2004-12-21

Family

ID=9946616

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2003001076A PE20040779A1 (en) 2002-10-25 2003-10-23 DERIVATIVES OF 1- (4-BENZYL-PIPERAZIN-1-IL) -3-PHENYL-PROPENONE

Country Status (19)

Country Link
US (1) US7645760B2 (en)
EP (1) EP1558594A2 (en)
JP (1) JP2006505575A (en)
KR (1) KR20050065620A (en)
CN (2) CN101570517A (en)
AR (1) AR043055A1 (en)
AU (1) AU2003296559B2 (en)
BR (1) BR0315662A (en)
CA (1) CA2502633C (en)
EC (1) ECSP055745A (en)
GB (1) GB0224917D0 (en)
MX (1) MXPA05004348A (en)
NO (1) NO20052487D0 (en)
PE (1) PE20040779A1 (en)
PL (1) PL374893A1 (en)
RU (1) RU2347782C2 (en)
TW (1) TW200420545A (en)
WO (1) WO2004037796A2 (en)
ZA (1) ZA200502700B (en)

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EP2938347A4 (en) * 2012-12-30 2016-08-10 Hadasit Med Res Service Use of alginate compositions in preventing or reducing liver damage caused by a hepatotoxic agent
EA035256B1 (en) 2013-07-18 2020-05-21 Новартис Аг Autotaxin inhibitors comprising a heteroaryl-benzyl-amide core
US10196369B2 (en) * 2013-09-26 2019-02-05 Sanford Burnham Prebys Medical Discovery Institute Spirocyclic EBI2 modulators
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Also Published As

Publication number Publication date
CA2502633A1 (en) 2004-05-06
ECSP055745A (en) 2005-07-06
PL374893A1 (en) 2005-11-14
JP2006505575A (en) 2006-02-16
CN101570517A (en) 2009-11-04
GB0224917D0 (en) 2002-12-04
AU2003296559A1 (en) 2004-05-13
RU2005115964A (en) 2006-01-27
TW200420545A (en) 2004-10-16
CA2502633C (en) 2011-02-01
ZA200502700B (en) 2006-05-31
CN100554257C (en) 2009-10-28
EP1558594A2 (en) 2005-08-03
MXPA05004348A (en) 2005-08-02
NO20052487L (en) 2005-05-24
WO2004037796A3 (en) 2004-06-17
WO2004037796A2 (en) 2004-05-06
AU2003296559B2 (en) 2007-11-01
CN1708489A (en) 2005-12-14
AR043055A1 (en) 2005-07-13
KR20050065620A (en) 2005-06-29
US20060173004A1 (en) 2006-08-03
US7645760B2 (en) 2010-01-12
RU2347782C2 (en) 2009-02-27
NO20052487D0 (en) 2005-05-24
BR0315662A (en) 2005-08-30

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